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In the post-pandemic deluge of devices, edtech platforms, and generative AI tools, this qualitative study examines how district leaders guide educational technology efforts to promote equity. Across six diverse secondary districts, analysis includes interviews, board/strategy documents, edtech investments, and platform inventories to trace decision logics, implementation routines, and equity impacts. A hybrid theoretical framework integrating Applied Critical Leadership and Educational Systems Change guided the cross-case synthesis. Findings surface vision–practice gaps, professional-learning bottlenecks, ambivalence about AI’s benefits/risks, and incremental equity moves (e.g., accessibility and translation tools). The project yields actionable outputs (equity-weighted procurement rubrics, bias-audit heuristics, integrated PD designs) and mid-range recommendations on how leaders convert technological overwhelm into durable, equitable outcomes.